Decrepit Desires

Author Note: This is another "Quick Stroke" story. Less world-building and character-building, quicker jump into the action, meant for...well...quickly getting off. This is the second short story I've done, I'm still experimenting with this style in between larger chapters of my other work. Hope you enjoy it.

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"So, tell me again who I'm supposed to play tonight?" Michael asked from the driver's seat. He was focused on the road as they drove downtown to a pub close to where Jennifer worked.

Jennifer felt herself grow wet at the question and subconsciously rubbed her thighs together, "It doesn't matter. That's the point really. Just some random person, some stranger taking what they want in a dark alley."

She ran her hand over her husband's crotch, "...taking me."

Jennifer felt how hard he was through his pants. She didn't want to admit out loud the type of person she fantasized about in this scenario. She wasn't sure what Michael would think about his prim and proper younger wife fantasizing about a homeless man taking her, running his dirty hands over her clean body. She shuddered at the mere thought.

"Hmmmm," Michael moaned softly, feeling his wife's manicured fingers teasing his shaft, "I like the sound of that."

"Bad boy," Jennifer responded. "Tonight is about my fantasy... maybe after we can discuss fulfilling yours."

Michael tore his eyes from the road to quickly look at his stunning wife. "Uh, really?"

She continued to lightly stroke his shaft while staring deep into his eyes. "We can talk about it. If we find the right guy for the job, I'll consider letting it happen while you watch."

To date, both of their fantasies had stayed strictly in the bedroom, but with some encouragement tonight they were acting out hers. The least she could do was consider his. He knew it would still take a bit of work to get her there.

She could tell her husband was getting very aroused from the sound of his breathing, and the way his eyes were roaming her body. "Eyes on the road, mister."

Her husband tore his eyes from her and focused them back on the road in front of them. For the rest of the drive, he was lost in thought.

They pulled over into a small parking lot next to Jennifer's office building. It was a nice summer night, warm but not too hot. Jennifer was wearing a loose black dress with spaghetti straps that ended mid-thigh, showing a lot of smooth leg. The tops of her breasts were on display, pushing against the material of the dress, threatening to spill out for all to see. Her long-toned legs were framed by the black stiletto high heels she wore.

Michael rounded the back of the car and took Sarah's hand as they began to walk towards the pub. He was dressed in jeans with a simple polo shirt.

As they crossed the parking lot a figure was shambling in their direction, weaving between the cars. The young couple tried to ignore the homeless man who was now in their vicinity. A horrible hacking cough emanated from the rough-looking individual. "Eh, got any change?"

Jennifer's eyes quickly darted to look the man over. She vaguely recognized him as a local homeless man living on these streets. He was wearing stained baggy sweatpants and old shoes that looked like they were ready to fall apart. His black faded t-shirt was full of holes and stains but was partly covered by what looked like a relatively newer denim jeans jacket. While it looked newer than the rest of his outfit, it was still poorly cared for. The man reeked of booze and had tattoos on one of his hands, a letter on each knuckle that collectively spelled out 'C-A-S-H'. The man's face looked like a leather glove that had been left out in the sun. He had what looked like a permanent scowl covered by white wispy facial hair. He clearly hadn't shaved in the last few weeks and it looked like he had all but given up on his bushy eyebrows. His eyes were intense and desperate, one slightly larger than the other. His look was hungry and focused on her body. Jennifer felt herself sliding closer to Michael, even as her panties grew curiously wet.

"Sorry, mate, no change on us," Michael replied as he kept his body between Jennifer and this older vagrant who was accosting them in the parking lot. He looked to be at least twenty years older than Michael.

They managed to get past him without incident. But, just as they had gotten several feet beyond him, he shouted after them, "Yeah! Can't hide any change in a dress like that, what an ass on her. JESUS FUCKING CHRIST!"

Michael tightened his grip on Jennifer's hand reassuringly as they stepped out of the parking lot onto the sidewalk. They could hear the old tramp dragging his feet and muttering to himself as they left him behind.

The walk to the pub was quiet, both of them running through the details of acting out Jennifer's fantasy in their heads.

"Is this the alley?" Michael asked as they stopped before the pub. Jennifer emerged from her thoughts to look down the long alley that ran next to the pub. Although the sun was just beginning to set, the alley already looked dark and dangerous. She'd walked down it years earlier when she had been interning with her company while she was still in college. She'd had drinks with a group of the older women she worked with and the group of them had all heard a noise - it was a woman moaning. Jennifer still remembered her head snapping around to see a homeless couple openly having sex in the alley - as if it was their personal space. The other women she was with had all run away quickly, giggling. In their embarrassed haste, they'd left Jennifer, who was still gawking at the rutting tramps, behind. Jennifer had studiously avoided porn before that, so the sight of this bum fucking a bag lady had been the first time she'd ever watched anyone having sex. The woman had twitched and her head had swung around - and her eyes had locked with those of the young intern. She then screamed a string of profanities as her mouth opened in an almost toothless smile. Jennifer would later realize that she was witnessing the first orgasm she'd ever seen, followed quickly by the second as the homeless man shook and spasmed. The man pulled his member out of the woman and turned to face Jennifer. She remembered thinking at first that it was a large flashlight or club hanging out of his pants.

"You want?" the man said, as he began to walk toward her, his dirty dripping phallus already beginning to harden again. That was when one of her coworkers had returned and grabbed her arm and they had gotten out of there. Jennifer had thought about that question over and over in the years since it was first asked. Did she want? Sex with Michael was good, but something about the street sex she'd seen had continued to intrigue her, maybe even obsess her, over all that time. Lately, there had been more homeless around the area of town she worked in, which is probably what had brought this fantasy flaring back to the forefront of her mind. She'd been toying with it for years now.

From their vantage point, they couldn't see much; the alley's darkness was deeper than the lighting conditions could easily explain, almost impenetrable in its uncanny depth. Despite the warm night, goosebumps ran over Jennifer's skin as the time for committing to her fantasy drew nigh.

"Yes. This is it," Jennifer finally responded to Michael's question. "Let's head inside and grab a booth."

***

Meanwhile, the bum whose tattoo identified him as 'Cash' shuffled through the parking lot, trying the handles of each car he passed. The first one he tried was locked, so he relieved himself on the car door out of spite. After a few more tries, he finally found one that was unlocked and he slid into the driver's seat. He rummaged around the contents of the glove box and found a pack of cigarettes, a lighter and some change.

He immediately lit up a cigarette, letting the nicotine wash into his system. He grabbed a battered steel flask from the breast pocket inside his denim jacket and took a long swig. Cash took another drag of the cigarette and exhaled into the cab of the car, smoke settling into the fabric.

Cash's grubby hands settled onto his hardening cock under his sweatpants. He reached under the waistband and began to stroke it in this stranger's car. He was thinking about the sweet pair of tits on that hot bitch in the black dress, how they were almost spilling out on display for him. And the sway of her hips as she walked away and the way her black dress fell on her perfect ass. He swore he could rest a drink on that thing. He bet it tasted like vanilla ice cream.

He had recognized her immediately but had never seen the guy she was with before. He'd noticed her several times when she'd been out and about during the daytime with other well-to-do women. Invariably, they had ignored him when he would catcall or ask for change. He'd rubbed more than one out to her over the past few months. He was thankful he now had more material for this purpose.

Cash settled back into the seat of the car, the cigarette now hanging limply out of his mouth, as he began tugging his cock at the thought of the hot bitch in the black dress.

***

Jennifer and Michael had been sitting in the bar for over two hours. Several pints had come and gone and both were feeling the effects.

Michael took a long drink of his beer and looked across his glass at his wife. She was giving him her 'fuck me' eyes and he knew it would soon be time to enact her fantasy. Did she really mean what she'd said? Would my fantasy be next?

"So," Jennifer mewed as she seductively ran her fingers along the rim of her empty glass, "let's just go over it one more time."

She raised a suggestive eyebrow at him and looked deep into his eyes. Her piercing green eyes always made his heart skip a beat, "I'm going to head into the back hallway and then slip out the door to the alley. You count to sixty and then come find me. I'll be bent over, exposed, waiting for you to come take me."

Michael gulped and took another large sip of his beer.

"I don't want any sweet talk, nothing. On second thought, don't say anything, just come up behind me and shove that cock of yours in and fuck my brains out." Her eyes locked with his, making sure he understood.

"Oh, I can do that." Michael surreptitiously ran his hand over the pocket in his pants. He felt the outline of the condom. He'd have to figure out when he could slip it onto his cock between the door from the bar and when he got behind her. He was always quite careful about making sure they didn't end up with any surprises; maybe in a few months when work had settled down some, they could resume their talks about starting a family.

Michael didn't bring up the condom. He knew it would ruin the mood as it had been a sore subject in the past. Jennifer had been annoyed at his refusal to stop using them, even after they had gotten married. She said she just wanted to feel his passion, for him to lose himself in her, consequences be damned. Her last comments along those lines had been a few months back now, but he still knew to tread lightly. He hoped his use of the condom wouldn't detract from her fantasy tonight.

"You going to finish that drink?" Sarah licked her lips and looked at him like a piece of meat.

"Yes, ma'am," Michael replied, downing the rest of his pint.

Jennifer smiled and stood up, bracing herself against the table as she discovered that the drinks had affected her equilibrium. "Count to sixty and then come find me."

With that, his wife turned on her heel and walked across the crowded bar until she was gone from sight. Michael took out his cell phone and watched the time, staring intently at the device until the next minute appeared.

Michael rose, trying to conceal his suddenly burgeoning erection as he moved towards the back area of the bar. As he was about to round the corner a heavy Scottish voice rang out behind him.

"Oi! Bucko. Not gonna dine and ditch, are ye?" Michael spun around to see the beefy bartender leering at him.

"No, just going to hit the head," Michael started to turn back towards the toilets.

"And what about that lass of yours? Where'd she disappear to?" The large man was glowering at Michael with a raised eyebrow. "First you come over here and settle your tab and then you can go take a piss," the bartender demanded.

"Okay, fine," Michael said, taking his wallet out and moving to the bar. "Let's just be quick about it."

***

Bent over a stack of long-forgotten pallets, Jennifer waited with anticipation for Michael to come take her. She'd stumbled upon this alcove after carefully navigating the dark alley. She was a few yards down from the pub's exit to the alley, away from the streetlights. Hopefully, it wouldn't be too difficult for Michael to find her in the dark. The cool air on her pussy reminded her how wet and exposed she was, sending even more of her fluids to the area. She felt a bead of moisture roll down her thigh.

She heard the sounds of slow, shuffling feet coming in her direction. Michael was getting close. She bit her lip and purposely thrust her ass out a bit more, her manicured nails gripping the wood of the pallet. She dug her heels into the alley's asphalt, bracing herself for what would come next.

The footsteps stopped close by. He must have spotted her. She knew how appetizing she must look, bent over and waiting for him. Now the footsteps resumed, quickening their pace until they came to a halt just behind her. She couldn't see him, but she could feel his presence. She thought she heard him sniffing and could feel his breath on her right ass cheek.

Then she felt the warmth of fingertips graze the outside of her thighs as her husband started to raise her dress. Jennifer felt the night's air touch her naked ass cheeks as Michael raised her dress higher.

She gripped the pallet tightly, and hung her head, completely giving her body up to her husband. His thumbs hooked under the sides of her thong and roughly yanked it down her thighs.

Her wet thong hung limply around her knees as she heard him shuffling behind her, centering himself. Jennifer jumped as she felt a muscular tongue licking her ass, leaving trails of saliva. She felt like her pussy was drenched, aching for his cock.

A strong hand pushed down on the small of her back. She felt her husband's cock push past her thighs, searching for her opening. Jennifer shifted her hips, helping to guide him into her.

Without a whisper of romance, her husband pretended to be a stranger, his cock was roughly shoved to its full length inside of her.

"Oh, fuck," Jennifer moaned, gripping onto the pallet harder to brace herself t as she was unceremoniously fucked in the darkness of the alleyway. Perhaps it was the alcohol, the situation or the animalistic angle at which he was taking her, but Michael had never made her feel so full before. He was really getting into this fuck, forcefully thrusting and withdrawing in complete strokes. She could hear the slaps of his pelvis into her ass cheeks, his grunting in rhythm as he drove into her, the splatting of her fluids as he slammed against her again and again.

Another thought passed through her mind. That's his bare cock. Finally! He isn't wearing a condom.

***

Michael watched the ancient debit machine screen spin, processing his card. It was taking forever to complete the transaction. Not to mention that the bartender had served a couple of customers before totalling up his drinks.

'Accepted' finally appeared on the screen and the machine printed out a receipt.

"Alright!" Michael said loudly over the sound of the music and crowd, the beefy bartender's back turned toward him. "All settled up. Have a good night."

The bartender peered over his shoulder and made a "come here" motion with his finger. Michael tried to keep the impatience off his face as he leaned over to hear what the man had to say.

"Don't let your woman out your sight around this place, laddie. Lotsa bad stuff happenin' lately. Lotsa baddies out there."

Michael smirked, unworried, and produced a twenty, laying it on the bar. "Thanks for the tip, man. Keep the change." The bartender shook his head slightly, realizing Michael was probably too drunk to listen to him. He turned his attention back to the young ladies sitting at the bar.

Michael quickly hurried down the back hallway and threw open the alleyway door.

***

Cash's dirty hands sank into the pale flesh of the hot brunette bent over in the alleyway for him. He had smelled pussy, and at first, he thought it was old Binzie trying to set up her ambush trick again, but the ass was too perfect to be her. He couldn't believe his luck but sometimes the streets just handed you a gift. He grunted, feeling his old cock sliding in and out of the young woman.

Her pussy gripped his cock, trying to pull more of him into her. He wasn't about to complain.

"Mhmmmm," she moaned as the tip of his bare cock pushed as far into her as it would go, "Fuck."

Cash gritted his teeth and smiled. He waited years to prove to himself that he could please one of these privileged women he saw in his neighborhood and now was his opportunity to show one of them just how much he could please her.

"Oh fuck, baby, don't stop, I'm so close. So close," Jennifer moaned. She could feel her orgasm rapidly building, the extra fullness of her husband's cock and the thrill of the dirty alley around her was pushing her body into overdrive. The sordid smell of cigarettes, booze and the undercurrent of trash was pushing her arousal far past what she'd expected.

Cash was enjoying the sensations of young pussy on his cock for the first time in decades. His eyes were darting around frantically as he bit his tongue in excitement. This bitch had put her naked ass out in Cash's alley and Cash was going to give her what she was waiting for. Cash was going to drop a load of his homeless cum into her.

He eyed the spaghetti straps on her shoulders and quickly began to lower them. Jennifer responded by lazily moving her arms until the straps were down by her sides. Cash grinned and reached around and roughly grabbed a handful of her breasts, while his other hand gripped the base of her neck for leverage.

The rough handling of her body was too much for her. Jennifer's orgasm finally exploded and washed over her body.

***

Michael peered into the darkness of the alley, unsure which direction to head. He had just exited the door and his eyes were still adjusting. Down to his left, he could see the streetlights and wondered if Jennifer had gone in that direction. To his right it was much darker, he didn't know if she would risk going down there.

As if on cue he heard a familiar sound.

"Mmmmmmmhmmmmmmm," it sounded like Jennifer. The sound she made when he was able to make her cum in bed. She must have taken matters into her own hands while he'd gotten held up by the bartender. The sound came from the darker end of the alley. He moved in that direction, following the unmistakable sounds of his wife pleasuring herself. His footsteps slowed with his uncertainty, as he also began to hear the fleshy slaps of bodies colliding.

As he rounded a corner and came across a small alcove he stopped dead in his tracks. His heart suddenly beating out of his chest in time with the couple's rutting.

Jennifer was bent over a stack of wooden crates as some dirty, smelly homeless man was fucking her from behind.

"Oh, fuck," his wife moaned as the man's cock pistoned in and out of her. "Don't fucking stop. Uh. Right there. Right there." Then she moaned, unintelligibly, clearly in the throes of ecstasy.

Michael took a step forward and stopped again. He was here to enact his wife's fantasy but he had inadvertently stumbled upon a version of his own. His brain was having trouble processing what he was seeing and trying to figure out how to react to the situation. His cock was hard in an instant, even though he was totally confused as to how Jennifer had gotten herself into the situation that he was witnessing.